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Volumn 53, Issue 39, 1997, Pages 13427-13448

Experimental and theoretical studies on the diastereoselective Diels-Alder reactions of chiral 1-alkoxy-1,3-butadienes. I: Parent system and 4-substituted derivatives

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE;

EID: 0030880292     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00854-5     Document Type: Article
Times cited : (8)

References (42)
  • 21
    • 0343374935 scopus 로고    scopus 로고
    • For an exception, see ref. 1a-c
    • For an exception, see ref. 1a-c.
  • 22
    • 0001685022 scopus 로고
    • Alkoxyacetylenes containing very bulky alkoxy groups are readily available from either ethyl vinyl ether or trichloroethylene: a) M.A. Pericàs, F. Serratosa, E. Valentí. Tetrahedron 1987, 43, 2311-2316.
    • (1987) Tetrahedron , vol.43 , pp. 2311-2316
    • Pericàs, M.A.1    Serratosa, F.2    Valentí, E.3
  • 29
    • 0343374929 scopus 로고    scopus 로고
    • note
    • 13C-NMR and HPLC when the reaction was performed at room temperature
  • 30
    • 0343374928 scopus 로고    scopus 로고
    • note
    • 3a on the basis of NOE experiments, has assumed that the analogous 2-methyl substituted diene preferentially exists in solution as a s-trans conformer and has subsequently assigned the configuration of the major diastereomers arising from the Diels-Alder reaction with MA and PTAD by assuming an endo attack to the more sterically free face of the diene in that conformer. We have now found that an AMI based theoretical conformational analysis supports this hypothesis. However, the small value of the calculated energy differences between conformer X (s-trans) and conformer IX (s-cis) suggests the convenience of a more detailed analysis.
  • 34
    • 0343374926 scopus 로고    scopus 로고
    • MacSpartan Plus, version 1.0, Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, California, 92612
    • MacSpartan Plus, version 1.0, Wavefunction, Inc., 18401 Von Karman, Suite 370, Irvine, California, 92612.
  • 35
    • 0030467165 scopus 로고    scopus 로고
    • For a recent theoretical account on the Diels-Alder reactions of (E)-1-amino-and (E)-1-hydroxy-1,3-butadiene with cyanoetylenes, see: Sustmann, R.; Sicking, W. J. Am. Chem. Soc. 1996, 118, 12562-12571.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12562-12571
    • Sustmann, R.1    Sicking, W.2
  • 39
    • 0001285938 scopus 로고
    • Ort, O. Org. Synth. 1987, 62, 203-214.
    • (1987) Org. Synth. , vol.62 , pp. 203-214
    • Ort, O.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.